Hello,
I'm an experienced apex developer, but it has always been in an existing environment. What is the easiest webserver configuration with the apex listener to get up and running without having to know a ton about system admin/server configurations? I looked briefly at Glassfish and WebLogic Server as it sounds like they play fairly nicely with Apex. Any pros or cons to either or other suggestions?

Many moons ago on my own laptop I initially started with Oracle's HTTP server, then moved to Glassfish, and now that the APEX Listener standalone is available - that is by far the easiest, thinnest option to get get going.

I think this describes exactly how simple it is to get going - one batch script with two commands (windows)
http://www.grassroots-oracle.com/2013/03/apex-listener-201-available.html